A selective intramolecular aldol condensation directed by a bifunctional enzyme mimic

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2541-2544

  Breslow, Ronald ^a   Desper, John ^a   Huang, Ying ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CYCLOPENTANE DERIVATIVE; HYDROXYALDEHYDE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029883733     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00337-1     Document Type: Article

References (4)

1. Breslow, R.; Graff, A. J. Am. Chem. Soc. 1993, 115, 10988.
2. Desper, J.M.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 12081.
3. HNMR: 7.36 (d, 2H), 7.22 (d, 2H), 3.90 (t, 1H), 3.82 (dd, 1H), 3.69 (dd, 1H), 2.94 (q, 1H), 1.4-2.2 (m, 5H), 1.32 (s, 9H) ppm. The stereochemistry is assigned from the finding of an NOE at 3.90 ppm and 1.75 ppm when 7.22 is irradiated, indicating that the phenyl ring is trans to the OH, and the fact that the proton at 3.90 is coupled to two protons with J=9.1 Hz for each, suggesting that both protons next to the CHOH group are trans to its proton.
4. Isomer 9A HNMR: 7.41 (d, 2H), 7.28 (d, 2H), 4.34 (t, 1H), 3.59 (d, 1H), 3.40 (d, 1H), 1.7-2.2 (m, 6H), 1.32 (s, 9H) ppm. NOE between 7.28 and 4.34. Isomer 9B HNMR: 7.41 (d, 2H), 7.38 (d, 2H), 4.61 (t, 1H), 4.00 (d, 1H), 3.73 (d, 1H), 1.5-2.2 (m, 6H), 1.33 (s, 9H) ppm. No NOE between 7.38 and 4.61.